Vinylene-linked covalent organic frameworks with manipulated electronic structures for efficient solar-driven photocatalytic hydrogen production

doi:10.1016/S1872-2067(23)64397-9

Abstract

Abstract:

Vinylene-linked covalent organic frameworks (COFs) are promising photocatalysts owing to their fully conjugated skeletons that facilitate charge carrier mobility. Constructing donor-acceptor (D-A) architectures could further enhance photoinduced charge generation and transport, thus promoting photocatalysis. Therefore, three D-A-type vinylene-linked COFs were fabricated via Knoevenagel polymerization for efficient photocatalysis. By varying the donor moieties from phenyl to 2,5-dimethylbenzene and 3,3'-dimethyl-1,1'-biphenyl in the skeletons, the light-harvesting, optical-bandgap, and charge-transfer properties of the COFs were precisely regulated. All three COFs exhibited attractive photocatalytic hydrogen evolution rates (HERs) upon visible-light irradiation, especially that fabricated using 2,4,6-trimethyl-1,3,5-triazine (TM) and 3,3'-dimethyl[1,1'-biphenyl]-4,4'-dicarboxaldehyde (DMA, TM-DMA-COF). TM-DMA-COF exhibited the strongest D-A interactions, excellent charge-carrier separation and transfer kinetics, and a reduced energy barrier for H₂ formation. Thus, it afforded the highest HER of 4300 µmol h^‒1 g_cat^‒1, surpassing those of most state-of-the-art COF photocatalysts. This study provides a simple and effective protocol for modulating the photocatalytic activities of COFs at the molecular level and an interesting insight into the relationship between structural design and photocatalytic performance.

Key words: Covalent organic framework, Photocatalytic H₂ generation, Olefin linkage, Porous polymer, Donor-acceptor

Zhipeng Xie, Xiubei Yang, Pei Zhang, Xiating Ke, Xin Yuan, Lipeng Zhai, Wenbin Wang, Na Qin, Cheng-Xing Cui, Lingbo Qu, Xiong Chen. Vinylene-linked covalent organic frameworks with manipulated electronic structures for efficient solar-driven photocatalytic hydrogen production[J]. Chinese Journal of Catalysis, 2023, 47: 171-180.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64397-9

https://www.cjcatal.com/EN/Y2023/V47/I4/171

Figures/Tables 4

Fig. 1. Synthesis and characterization of COFs. (a) Schematic synthetic routes of TM-TA-COF, TM-MA-COF, and TM-DMA-COF. Experimental (red), Pawley-refined (purple circles), simulated powder X-ray diffraction patterns of AA (orange) and AB (green) stacking, and difference curves (black) of TM-TA-COF (b), TM-MA-COF (c), and TM-DMA-COF (d). Top and side views of TM-TA-COF (e), TM-MA-COF (f), and TM-DMA-COF (g). N2 sorption isotherms at 77 K for TM-TA-COF (h), TM-MA-COF (i), and TM-DMA-COF (j). Inset: pore-size distribution.

Fig. 2. (a) UV-vis DRS profiles of TM-TA-COF (black), TM-MA-COF (green), and TM-DMA-COF (cyan). Integrated PL emission intensity as a function of temperature from 100 to 300 K (Inset: temperature-dependent PL spectra) for TM-TA-COF (b), TM-MA-COF (c), and TM-DMA-COF (d).

Fig. 3. (a) Photocatalytic HERs of the obtained COF samples. (b) Photostability test of TM-DMA-COF for photocatalytic H2 evolution. Electrostatic potential surfaces (c) and HOMO-LUMO distributions (d) of TM-TA-COF, TM-MA-COF, and TM-DMA-COF.

Fig. 4. Calculated molecular structures and average Bader charges (a negative value indicates electron gain. Higher absolute values indicate stronger electron-withdrawing abilities) of donor moieties in TM-TA-COF (a), TM-MA-COF (b), and TM-DMA-COF (c). The total densities of states (TDOSs) and partial densities of states (PDOSs, red and blue for fragments 1 and 2, respectively) in each defined fragment of TM-TA-COF (d), TM-MA-COF (e), and TM-DMA-COF (f). The free-energy variations for the H2 evolution at each active site of TM-TA-COF (g), TM-MA-COF (h), and TM-DMA-COF (i).

References

[1]	X. Wang, L. Chen, S. Y. Chong, M. A. Little, Y. Wu, W. H. Zhu, R. Clowes, Y. Yan, M. A. Zwijnenburg, R. S. Sprick, A. I. Cooper, Nat. Chem., 2018, 10, 1180-1189.
[2]	J. Chen, X. Tao, L. Tao, H. Li, C. Li, X. Wang, C. Li, R. Li, Q. Yang, Appl. Catal. B, 2019, 241, 461-470.
[3]	E. Jin, Z. Lan, Q. Jiang, K. Geng, G. Li, X. Wang, D. Jiang, Chem, 2019, 5, 1632-1647.
[4]	Z. Wang, C. Li, K. Domen, Chem. Soc. Rev., 2019, 48, 2109-2125.
[5]	K. Sivula, R. V. D. Krol, Nat. Rev. Mater., 2016, 1, 15010.
[6]	R. S. Sprick, B. Bonillo, R. Clowes, P. Guiglion, N. J. Brownbill, B. J. Slater, F. Blanc, M. A. Zwijnenburg, D. J. Adams, A. I. Cooper, Angew. Chem. Int. Ed., 2016, 55, 1792-1796.
[7]	L. Wang, Y. Zhang, L. Chen, H. Xu, Y. Xiong, Adv. Mater., 2018, 30, 1801955.
[8]	G. B. Wang, S. Li, C. X. Yan, Q. Q. Lin, F. C. Zhu, Y. Geng, Y. B. Dong, Chem. Commun., 2020, 56, 12612-12615.
[9]	W. Chen, L. Wang, D. Mo, F. He, Z. Wen, X. Wu, H. Xu, L. Chen, Angew. Chem. Int. Ed., 2020, 59, 16902-16909.
[10]	C. Wang, H. Zhang, W. Luo, T. Sun, Y. Xu, Angew. Chem. Int. Ed., 2021, 60, 25381-25390.
[11]	T. Zhou, L. Wang, X. Huang, J. Unruangsri, H. Zhang, R. Wang, Q. Song, Q. Yang, W. Li, C. Wang, K. Takahashi, H. Xu, J. Guo, Nat. Commun., 2021, 12, 3934.
[12]	Q. Wang, K. Domen, Chem. Rev., 2020, 120, 919-985.
[13]	Y. Fang, Y. Hou, X. Fu, X. Wang, Chem. Rev., 2022, 122, 4204-4256.
[14]	A. Nagai, X. Chen, X. Feng, X. Ding, Z. Guo, D. Jiang, Angew. Chem. Int. Ed., 2013, 52, 3770-3774.
[15]	L. Stegbauer, K. Schwinghammer, B. V. Lotsch, Chem. Sci., 2014, 5, 2789-2793.
[16]	Z. Li, Y. Zhi, P. Shao, H. Xia, G. Li, X. Feng, X. Chen, Z. Shi, X. Liu, Appl. Catal. B, 2019, 245, 334-342.
[17]	H. Wang, H. Wang, Z. Wang, L. Tang, G. Zeng, P. Xu, M. Chen, T. Xiong, C. Zhou, X. Li, D. Huang, Y. Zhu, Z. Wang, J. Tang, Chem. Soc. Rev., 2020, 49, 4135-4165.
[18]	R. Chen, Y. Wang, Y. Ma, A. Mai, X. Y. Gao, L. Gao, L. Qiao, X. B. Li, L. Z. Wu, C. Wang, Nat. Commun., 2021, 12, 1354.
[19]	S. Ma, Z. Li, J. Jia, Z. Zhang, H. Xia, H. Li, X. Chen, Y. Xu, X. Liu, Chin. J. Catal., 2021, 42, 2010-2019.
[20]	Y. Li, X. Song, G. Zhang, L. Wang, Y. Liu, W. Chen, L. Chen, ChemSusChem, 2022, 15, e202200901.
[21]	L. Sun, L. Li, J. Yang, J. Fan, Q. Xu, Chin. J. Catal., 2022, 43, 350-358
[22]	L. Sun, M. Lu, Z. Yang, Z. Yu, X. Su, Y. Lan, L. Chen, Angew. Chem. Int. Ed., 2022, 61, e202204326.
[23]	Z. Liang, R. Shen, P. Zhang, Y. Li, N. Li, X. Li, Chin. J. Catal., 2022, 43, 2581-259.
[24]	T. Zhang, G. Zhang, L. Chen, Acc. Chem. Res., 2022, 55, 795-808.
[25]	P. Dong, A. Zhang, T. Cheng, J. Pan, J. Song, L. Zhang, R. Guan, X. Xi, J. Zhang, Chin. J. Catal., 2022, 43, 2592-2605.
[26]	F. Zhang, X. Li, X. Dong, H. Hao, X. Lang, Chin. J. Catal., 2022, 43, 2395-2404.
[27]	D. Song, W. Xu, J. Li, J. Zhao, Q. Shi, F. Li, X. Sun, N. Wang, Chin. J. Catal., 2022, 43, 2425-2433.
[28]	Z. Zhou, C. Bie, P. Li, B. Tan, Y. Shen, Chin. J. Catal., 2022, 43, 2699-2707.
[29]	S. Kandambeth, K. Dey, R. Banerjee, J. Am. Chem. Soc., 2019, 141, 1807-1822.
[30]	E. Jin, M. Asada, Q. Xu, S. Dalapati, M. A. Addicoat, M. A. Brady, H. Xu, T. Nakamura, T. Heine, Q. Chen, D. Jiang, Science, 2017, 357, 673-676.
[31]	H. Lyu, C. S. Diercks, C. Zhu, O. M. Yaghi, J. Am. Chem. Soc., 2019, 141, 6848-6852.
[32]	S. Wei, F. Zhang, W. Zhang, P. Qiang, K. Yu, X. Fu, D. Wu, S. Bi, F. Zhang,, J. Am. Chem. Soc., 2019, 141, 14272-14279.
[33]	A. Acharjya, L. Longworth-Dunbar, J. Roeser, P. Pachfule, A. Thomas, J. Am. Chem. Soc., 2020, 142, 14033-14038.
[34]	L. Zhai, S. Yang, X. Yang, W. Ye, J. Wang, W. Chen, Y. Guo, L. Mi, Z. Wu, C. Soutis, Q. Xu, Z. Jiang, Chem. Mater., 2020, 32, 9747-9752.
[35]	Y. Li, W. Cui, Q. Jiang, Q. Wu, R. Liang, Q. Luo, J. Qiu, Nat. Commun., 2021, 12, 4735.
[36]	F. Meng, S. Bi, Z. Sun, B. Jiang, D. Wu, J. S. Chen, F. Zhang, Angew. Chem. Int. Ed., 2021, 60, 13614-13620.
[37]	S. Wang, X. X. Li, L. Da, Y. Wang, Z. Xiang, W. Wang, Y. B. Zhang, D. Cao, J. Am. Chem. Soc., 2021, 143, 15562-15566.
[38]	Z. Wang, Y. Yang, Z. Zhao, P. Zhang, Y. Zhang, J. Liu, S. Ma, P. Cheng, Y. Chen, Z. Zhang, Nat. Commun., 2021, 12, 1982.
[39]	J. Hu, J. Zhang, Z. Lin, L. Xie, S. Liao, X. Chen, Chem. Mater., 2022, 34, 5249-5257.
[40]	S. Xu, Z. Liao, A. Dianat, S. W. Park, M. A. Addicoat, Y. Fu, D. L. Pastoetter, F. G. Fabozzi, Y. Liu, G. Cuniberti, M. Richter, S. Hecht, X. Feng, Angew. Chem. Int. Ed., 2022, 61, e202202492.
[41]	S. Bi, C. Yang, W. Zhang, J. Xu, L. Liu, D. Wu, X. Wang, Y. Han, Q. Liang, F. Zhang, Nat. Commun., 2019, 10, 2467.
[42]	R. Chen, J.L. Shi, Y. Ma, G. Lin, X. Lang, C. Wang, Angew. Chem. Int. Ed., 2019, 58, 6430-6434.
[43]	Y. Zhao, H. Liu, C. Wu, Z. Zhang, Q. Pan, F. Hu, R. Wang, P. Li, X. Huang, Z. Li, Angew. Chem. Int. Ed., 2019, 58, 5376-5381.
[44]	S. Bi, P. Thiruvengadam, S. Wei, W. Zhang, F. Zhang, L. Gao, J. Xu, D. Wu, J.S. Chen, F. Zhang,, J. Am. Chem. Soc., 2020, 142, 11893-11900.
[45]	S. Li, L. Li, Y. Li, L. Dai, C. Liu, Y. Liu, J. Li, J. Lv, P. Li, B. Wang, ACS Catal., 2020, 10, 8717-8726.
[46]	J. Shi, R. Chen, H. Hao, C. Wang, X. Lang, Angew. Chem. Int. Ed., 2020, 59, 9088-9093.
[47]	Y. Wang, W. Hao, H. Liu, R. Chen, Q. Pan, Z. Li, Y. Zhao, Nat. Commun., 2022, 13, 100.
[48]	S. Bi, Z. Zhang, F. Meng, D. Wu, J. S. Chen, F. Zhang, Angew. Chem. Int. Ed., 2022, 61, e202111627.
[49]	L. Zhai, Z. Xie, C. X. Cui, X. Yang, Q. Xu, X. Ke, M. Liu, L. B. Qu, X. Chen, L. Mi, Chem. Mater., 2022, 34, 5232-5240.
[50]	Z. Lan, W. Ren, X. Chen, Y. Zhang, X. Wang, Appl. Catal. B, 2019, 245, 596-603.
[51]	Z. Lan, G. Zhang, X. Chen, Y. Zhang, K. Zhang, X. Wang, Angew. Chem. Int. Ed., 2019, 58, 10236-10240.
[52]	Z. Lan, M. Wu, Z. Fang, X. Chi, X. Chen, Y. Zhang, X. Wang, Angew. Chem. Int. Ed., 2021, 60, 16355-16359.
[53]	G. Li, Z. Xie, Q. Wang, X. Chen, Y. Zhang, C. Wang, Chem. Eur. J., 2021, 27, 939-943.
[54]	S. Chai, X. Chen, X. Zhang, Y. Fang, R. Sprick, X. Chen,, Environ Sci.: Nano, 2022, 9, 2464-2469.
[55]	J. Xu, C. Yang, S. Bi, W. Wang, Y. He, D. Wu, Q. Liang, X. Wang, F. Zhang, Angew. Chem. Int. Ed., 2020, 59, 23845-23853.
[56]	J. F. Zheng, Z. P. Xie, Z. Li, Y. Chen, X. Fang, X. Chen, M. J. Lin, Dyes Pigm., 2021, 185, 108946.
[57]	T. Lu, F. Chen, J. Comput. Chem., 2012, 33, 580-592.
[58]	M. Melchionna, P. Fornasier, ACS Catal., 2020, 10, 5493-5501.
[59]	S. Cao, L. Piao, Angew. Chem. Int. Ed., 2020, 59, 18312-18320.
[60]	Z. Wang, T. Hisatomi, R. Li, K. Sayama, G. Liu, K. Domen, C. Li, L. Wang, Joule, 2021, 5, 344-359.
[61]	M. Qureshi, K. Takanabe, Chem. Mater., 2018, 29, 158-167.
[62]	S. M. H. Hejazi, M. Shahrezaei, P. Błonski, M. Allieta, P. M. Sheverdyaeva, P. Moras, Z. Badura, S. Kalytchuk, E. Mohammadi, R. Zboril, S. Kment, M. Otyepka, A. Naldoni, P. Fornasiero, Chem. Catal., 2022, 2, 1177-1190.
[63]	O. Bettucci, T. Skaltsas, M. Calamante, A. Dessì, M. Bartolini, A. Sinicropi, J. Filippi, G. Reginato, A. Mordini, P. Fornasiero, L. Zani, ACS Appl. Energy Mater., 2019, 2, 5600-5612.
[64]	M. Monai, M. Melchionna, P. Fornasiero, Adv Catal., 2018, 63, 1-73.
[65]	K. C. Christoforidis, Z. Syrgiannis, V. L. Parola, T. Montini, C. Petit, E. Stathatos, R. Godin, J. R. Durrant, M. Prato, P. Fornasiero, Nano Energy, 2018, 50, 468-478.
[66]	Y. Wang, A. Vogel, M. Sachs, R. S. Sprick, L. Wilbraham, S. J. A. Moniz, R. Godin M,. A. Zwijnenburg, J. R. Durrant, A. I. Cooper, J. Tang, Nat. Energy, 2019, 4, 746-760.
[67]	Y. Pellegrin, F. Odobel, C. R. Chim., 2017, 20, 283-295.
[68]	E. Mitchell, A. Law, R. Godin, J. Photochem. Photobiol. C, 2021, 49, 100453.
[69]	X. Xiao, Y. Gao, L. Zhang, J. Zhang, Q. Zhang, Q. Li, H. Bao, J. Zhou, S. Miao, N. Chen, J. Wang, B. Jiang, C. Tian, H. Fu, Adv. Mater., 2020, 32, 2003082.